Big, bad and sometimes untradeable NHL contracts

How much is too much? For NHL clubs, it seems the pay window is always open. And with Toronto Maple Leafs forward Phil Kessel putting pen to paper on an eight-year, $64 million deal Tuesday, the jury is open as to whether this was a smart signing or this will be a complete financial bust in a few years. Looking back, here are seven other high-priced deals NHL clubs later came to regret.

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Alexei Yashin, 10 years, $87.5 million: In what could be the worst trade-and-sign in league history, the Islanders swapped Zdeno Chara, forward Bill Muckalt and a second overall draft selection, which the Senators used to draft highly-touted centerman Jason Spezza, for the Russian forward. Isles general manager Mike Milbury then signed Yashin to an enormous 10-year, $87.5 million contract. His production level promptly sank, and he was bought out. He's still on the books through 2014-15. (QMI Agency file photo)

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Wade Redden, six years, $39 million: For a few years, the Rangers defenceman was known as the most expensive minor league player ever. The Blueshirts placed him on waivers and sent him down to their AHL affiliate after poor production (and to alleviate Redden's cap hit) after signing him to a mega-deal. He was finally bought out, and signed a $800,000 deal with the Blues last season, then he was traded to the Boston Bruins at the deadline. The 36-year-old free agent is still on the Rangers' books for another two years. (QMI Agency file photo)

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Ilya Kovalchuk, 15 years, $100 million: The Devils landed in hot water with the NHL after the league rejected the team's original contract of 17 years, $102 million due to cap issues. They had to pay a $3 million penalty to the NHL, gave up a third round draft choice in the 2011 NHL Entry Draft and also one future first round draft choice within the next four seasons. Ilya has since retired from the NHL and signed a comparable deal with SKA St. Petersburg in Russia. (QMI Agency file photo)

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Scott Gomez, seven years, $51.5 million: In another example of losing the goal scoring touch after a big signing, Gomez managed only 21 goals in the three years after lining his wallet with Montreal. Gomez was then bought out, played with the Sharks last season, and now plays for the Florida Panthers. (QMI Agency file photo)

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Rick DiPietro, 15 years, $67.5 million: In what is considered to be the worst sports contract in history, the Isles goalie inked a deal that earns him a modest $4.5 mil a season, but it lasts until 2021. You read correctly - 2021. (QMI Agency file photo)

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Ilya Bryzgalov, nine years, $51 million: Just when you thought the insane goalie contracts hit a high-water mark with Rick DiPietro, the Flyers went ahead and signed the Russian netminder to a deal that will cost Philly a cap hit of more than $5.6 million per season until 2020. (QMI Agency photo)

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Roberto Luongo, 12 years, $64 million: Even Bobby Lou admitted his contract was immovable. But now with Cory Schneider out of the picture, the 34-year-old goaltender is now the starter for the foreseeable future after Canucks GM Mike Gillis gave up on trading the former Hart Trophy winner. (QMI Agency photo)